Rational design of a fluorescent sensor to simultaneously determine both the enantiomeric composition and the concentration of chiral functional amines

Journal of the American Chemical Society
Kaili WenLin Pu

Abstract

A fluorescent molecular probe, a 1,1'-bi-2-naphthol (BINOL)-based bis(naphthylimine) compound (R)-4, is designed to exhibit very different fluorescent responses at two emission wavelengths toward a variety of chiral functional amines including diamines, amino alcohols, and amino acids. At one emission wavelength (λ1), it shows high sensitivity toward the substrates, and at another wavelength (λ2), it shows high enantioselectivity. This is the first rational design of such a dual responsive fluorescent sensor which can be used to simultaneously determine both the concentration and the enantiomeric composition of functional chiral amines by one fluorescent measurement. This strategy is potentially generally applicable for the construction of sensors for rapid assay of structurally diverse chiral substrates. When (R)-4 is treated with various chiral functional amines in the presence of Zn(OAc)2, its 2-naphthylamine units are displaced off to show large fluorescent enhancement at λ1 = 427 nm (I1) due to the restored emission of 2-naphthylamine. The combination of the remaining chiral binaphthyl unit with the chiral substrates leads to highly enantioselective fluorescent enhancement at λ2 > 500 nm (I2). Since I1 is only concentratio...Continue Reading

References

Mar 7, 2002·Journal of the American Chemical Society·Jing LinLin Pu
Mar 11, 2004·Chemical Reviews·Lin Pu
Jun 29, 2004·Angewandte Chemie·Jianzhang ZhaoTony D James
Nov 13, 2004·Journal of the American Chemical Society·Xuefeng Mei, Christian Wolf
Dec 3, 2010·Journal of the American Chemical Society·Shanshan Yu, Lin Pu
Apr 26, 2011·Topics in Current Chemistry·Alessandro AccettaRosangela Marchelli
Aug 13, 2011·Accounts of Chemical Research·Lin Pu
Sep 6, 2011·Chemical Society Reviews·Diana LeungEric V Anslyn
Feb 7, 2014·Chemical Reviews·Xin ZhangJuyoung Yoon

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Citations

Sep 4, 2015·Journal of the American Chemical Society·Yang YePeter J Stang
Oct 5, 2016·Journal of the American Chemical Society·Zeus A De Los Santos, Christian Wolf
Nov 5, 2016·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Yuan Jun GaoWei Jun Jin
Jan 28, 2017·Journal of the American Chemical Society·Samantha L PilicerChristian Wolf
Jun 14, 2017·Journal of the American Chemical Society·Li-Li WangWei Jiang
Jan 15, 2016·Organic & Biomolecular Chemistry·Zeus A De Los SantosChristian Wolf
Oct 12, 2017·Chemical Society Reviews·Di WuTony D James
Jun 28, 2019·Organic & Biomolecular Chemistry·Samantha L PilicerChristian Wolf
Sep 25, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Zheng Xu, Li-Wen Xu
Mar 1, 2016·Chemical Science·Ali AkdenizPavel Anzenbacher
Jul 21, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Lei ShiXiao-Qi Yu
Mar 30, 2021·Chemical Reviews·Jun Kee ChengBin Tan
May 11, 2021·Analytical Methods : Advancing Methods and Applications·Qianqian ZhaoYong Kong
Jun 25, 2021·Chemical Science·Runkun ZhangGongke Li
Jul 31, 2018·Journal of the American Chemical Society·Brenden T HerreraChristian Wolf
Feb 14, 2018·Analytical Chemistry·Darshan C PatelDaniel W Armstrong

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